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Using Outlook?
Outlook is a very popular email program among Windows users. Being a Microsoft product it tends to want to do things its own way. I'll address those issues in this article as they come to mind.

Quoting

What is quoting? It's when you reply to a message and you want to show the sender's comments near yours. This helps establish a context to your reply and keep the conversation flowing. However, most versions of Outlook don't handle quoting in a useful or expected way. Email has been around a very long time, much longer than Outlook. Most email programs indent the previous replies using a character like ">" or with a colored bar. Most installations of Outlook are not configured this way requiring you to resort to colors, caps, or italics to differentiate the conversation. Here's how you can fix this behavior:
  1. Choose Options from the Tools menu.
  2. Click on E-mail Options.
  3. Choose to "Prefix each line..." for replying and forwarding.
  4. Next to "Prefix each line with" enter "> " (include the space).
For more information see this article.

Outlook Alternatives

Besides general idiosyncrasies, Outlook has been tied to security exploits and other compatibility problems. There are many other email programs available as an alternative to Outlook. One of those options you should seriously consider is Mozilla's Thunderbird.